Resinous acid-amine condensation product and process of making the same



Patented Apr. 16, 1940 RESINOUS ACID-AWE CONDENSATION PRODUCT ANDPROCESS OF .MAKING THE SAME Almon G. Hovey, Pleasant Ridge, and TheodoreS. Hodgins, Royal Oak, Micla, assignors to Reichhold Chemicals,

Inc., formerly Beck,

Koller & Company, Inc., Detroit, Mich.

No Drawing. Application December 15, 1938, Serial No. 245,984

12 Claims.

The invention relates broadly to improvements in resinous acid-aminecondensation products and to the process of making the same, the presentapplication being a continuation-in-part of our co-pending applicationSerial No. 147,569, filed June 10, 1937, now Patent No. 2,153,801, datedApril 11, 1939, the disclosure of which is hereby incorporated byreference as part of the disclosure of the present application.

In the manufacture of alkyd resins it has been proposed to substitutethe polyhydric alcohols, in whole or in part by triethanolamine, whichis an hydroxylated amine, and to react such hydroxylated amine with anorganic carboxylic acid. In such reaction, however, the triethanolamineacts in a manner similar to glycerol and other polyhydric alcoholscustomarily employed in the manufacture of alkyd resins, owing to thepresence of the hydroxyl groups which react with the organic acid in thewell known manner.

It-has also been proposed to employ certain organic amines in minorproportion as modifying agents in connection with various otheringredients employed in the manufacture of synthetic products.Furthermore various polyamines have been reacted with certain organicacids.

We have discovered that valuable resinous condensation products havingdistinctive properties may be produced by fusing together hydroxyorganic acids and non-hydroxylated organic monoamines wherein the saidacids and amines constitute the sole or at least the principal reactingingredients.

The claims of the present application are directed specifically to thepreparation of resins from lactic acid and organic mono-amines such asisobutylamine, pyridine, dioctylamine and 'aniline, such resins beingfound to be commercially useful for various purposes.

The following specific examples are given by way of illustration and notby way of limitation.

Example 1 One mol of lactic acid was reacted with one 4' mol ofisobutylamine for 25 minutes at 80-205 C. wlthout much foaming. Theresulting dark red resin had a cure time of 1'! seconds at 200 C. on thehot plate. The resin was insoluble in water and mineral spirits andsoluble in acetone,

. alcohol and toluol. A 60% solution of the resin in alcohol had aGardner-Holdt viscosity at 25 C. of less than A and a Hellige-Klettcolor of 9.

Sample 2 5 One mol of lactic acid was heated with one mol of pyridinefor minutes at 105-160 C. without foaming, yielding a pale straw coloredresin having a cure time of 8 seconds at 200 C. on the hot plate. Theresin was soluble in water, acetone and alcohol; insoluble in toluol andmin- 5 cm! spirits.

Example 3 One mol of lactic acid was reacted with one mol ofdioctylamine for 25 minutes at 150-270 C., resulting in a pale strawcolored resin having a cure time of -22 seconds on the hot plate at 200C, This product was insoluble in water; soluble in acetone, alcohol,toluol and mineral spirits.

Example 4 One mol of lactic acid was reacted with one mol of aniline for12 minutes at 80-2l0 C. without foaming, producing a light yellow resinhaving a cure time of 15 seconds on the hot plate at :0 200 C. The resinis slightly soluble in water and toluol; soluble in acetone and alcoholand insoluble in mineral spirits.

We claim:

1. A resinous reaction product formed by fusing together lactic acid andan organic mono-amine selected from a group consisting of isobutylamine,pyridine, dioctylamine and aniline, said acid and said amine comprisingthe principal reacting ingredients.

2. A process which comprises fusing together lactic acid and an organicmono-amine selected from a group consisting of isobutylamine, pyridine,dioctylamine and aniline until a resinous condensation product isobtained, said acid and said amine comprising the principal reactiningredients.

3. A resinous reaction product formed by fusing together equimolecularquantities of lactic acid and isobutylamine, said acid and aminecomprising the principal reacting ingredients, said product being darkred in color having a cure time of about 17 seconds at 200 C. on a hotplate. and being soluble inacetone, alcohol and toluol.

4. M alcohol solution of the resin defined in claim 3, having aGardner-Holdt viscosity at 25 C, of less than A and a Hellige-Klettcolor of 9.

5. A process of producing a resinous condensation product whichcomprises fusing together one 50 mol of lactic acid and one mol ofisobutylamine for about 25 minutes at 20-205 C., said acid and saidamine comprising the principal reacting ingredients.

8. A pale straw-colored resin formed by heatso ing togetherequimolecular quantities of-lactic acid and pyridine, as the principalreacting ingredients.

7. A process of producing a resinous product which comprises heatingtogether one moi of lactic acid and one moi of'pyridine for about 10minutes at 105-160 C., said acid and said amine constituting theprincipal reacting ingredients.

8. A light yellow resin formed by fusing together equimolecularquantities of lactic acid and aniline, as the principal reactingingredients, said resin having a cure time oi. 15 seconds on the hotplate at 200 C., and being soluble in acetone and alcohol, insoluble inmineral spirits and slightly soluble in water and toluol.

9. A process of producing a resin which com-

